Haugwitz et al. in European Patent Application No. 95,584A disclose various N-substituted prolines having a diuretic moiety coupled directly to a 4-phenylthio or 4-phenoxy substituent on the proline ring.
Ondetti et al. in U.S. Pat. No. 4,105,776 disclose that various mercaptoacyl derivatives of proline, hydroxy substituted proline, and alkyl substituted proline are useful hypotensive agents due to their angiotensin converting enzyme inhibition activity.
Ondetti et al. in U.S. Pat. No. 4,316,906 disclose that mercaptoacyl derivatives of various ether and thioether substituted prolines are also useful hypotensive agents due to their angiotensin converting enzyme inhibition activity.
Horovitz et al. in U.S. Pat. No. 4,217,347 disclose reducing blood pressure by administering a composition including a diuretic and the mercaptoacyl proline compounds taught by Ondetti et al. in U.S. Pat. No. 4,105,776.
Yoshitomi in Belgian Pat. No. 879,158 disclose chlorosulfamoylbenzoylthiopropionyl prolines and thiazolidines as possessing diuretic and hypotensive activity.
Tanabe in European Patent Application No. 18,549 disclose angiotensin converting enzyme inhibitors having a carboxyethylcarbamoyl group attached to the N-atom of tetrahydroisoquinoline carboxylic acid and this same sidechain coupled to the N-atom of proline is disclosed in Japanese Application No. 5151-555.
Harris et al. in U.S. Pat. No. 4,374,829 disclose that various carboxyalkyl dipeptides are angiotensin converting enzyme inhibitors.
Petrillo in U.S. Pat. Nos. 4,168,267 and 4,337,201 disclose that various phosphinylalkanoyl prolines, substituted prolines, and their esters are angiotensin converting enzyme inhibitors.